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In the above example, would it be more correct to say:

"To whomever they were sent" or "To whomever they were sent to"?

Another example is:

"To what month is the event being deferred to?" Would it be more correct to simply ask "To what month is the event being deferred?"

I understand that it would be simpler in these examples to drop the first instance of "to". For example: "What month is the event being deferred to?" and "Whomever they were sent to". But I feel like the first "to" makes the sentence more formal. Disregarding formality and simplicity, would it be grammatically more accurate to include or drop the second instance of "to"?

3 Answers 3

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Yes, having two "to"s is redundant and incorrect.

There is a much-debated rule in English, "Never end a sentence with a preposition." I and many others think this is a silly and pointless rule, because following it often leads to sentences that are more awkward and difficult to understand than ignoring it. For example, most Americans would say, "Who did you send the package to?" But by this rule, you should say, "To whom did you send the package?" Winston Churchill is famously reported to have replied to someone who criticized him for breaking this rule by saying, "That is a rule up with which I shall not put." To ruin the joke by explaining it, most people would say, "That's a rule I won't put up with." But that breaks the rule because "with" is a preposition and ends the sentence. So instead Churchill gave the "legal" alternative to show how strained and silly it is. Personally, I often quote the rule as, "Never use a preposition to end a sentence with." (Get it? Hee hee.)

So ... By this silly rule, you should say, "To what month is the event being deferred?" But few people actually say that. Most people say, "What month is the event being deferred to?" Including both "to"s is just unnecessary.

Oh, aside from "you should follow this rule because somebody who called himself an expert wrote it in a book", I think the reason for the rule is this: A preposition has to have an object. If you say that you did something "with" or "to", for example, it doesn't make sense unless you tell us what it was with or what it was to. Normally the object of a preposition follows the preposition. So if the preposition ends the sentence, than it has no object and doesn't make sense.

The flaw in that argument is the word "normally". Yes, most of the time the object of a preposition follows the preposition. But not always. Like if I say, "We deferred the meeting to March", then "March" is the object of the preposition. All well and good. But sometimes we re-arrange the word order for emphasis. So I might say, "No, MARCH is the month that we deferred the meeting to." The object of the preposition "to" is "March". It's not that it doesn't have an object. It's just that the object is in a somewhat unusual place.

This rule is one of many (in grammar and many other aspects of life) where someone says, "Usually X causes Y. Therefore if you want Y to happen, you must always do X." That is, they casually shift from "usually" or "normally" or "often" to "always", or from "rarely" to "never".

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  • That's a very insightful answer and I had a lot of fun reading it, thanks! From your answer, I understand that in most cases it's better to not end a sentence with "to". Could you maybe look at Anton Sherwood's answer in this thread and my comment there and comment on these instances of using "to" as well?
    – Ferguson
    Jun 1, 2020 at 10:50
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It depends on the meaning. In your first fragment, the two tos might have different meanings: “The parcel belongs to whomever it was sent to” — that is, if the parcel was sent to Susan, then it also belongs to Susan, and neither to can be dropped. But because it invites confusion, such a sentence should be rephrased: “The parcel belongs to whoever properly received it” or “The parcel belongs to its addressee.”

Your second example is a complete sentence, in which there is no other verb to which the second to could be attached, so no apparent reason for it to be there.

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  • I wish I could work in a reference to “Live and Let Die”! Jun 1, 2020 at 3:05
  • In the first fragment, the to isn't out of place when the verb is "belongs" but if the verb is "go" (The parcel will go to whomever they were sent to), is the "to" still not redundant? I ask because the verbs "go" and "sent" are contextually closer than "belongs" and "sent". Further, by your answer I guess this statement is correct: Apprentices and child servants were contractually bound to whomever they were sent to but if we were to make a question out of it, will it be phrased as "To whom were they bound to"? or "To whom were they bound?" Thanks for the clarity!
    – Ferguson
    Jun 1, 2020 at 8:12
  • Yes, I would still use both ’to’s in such a sentence. — How is this question about a question different from your original question about a question? Jun 2, 2020 at 4:18
  • Sure, fair enough. It can be valid to have the word "to" twice in a sentence if it's performing two different functions or introducing two distinct prepositional phrases. "To know her is to love her." The trick is that you don't want to repeat a word when the second occurrence is redundant. Like, "Department of Redundancy Department".
    – Jay
    Jun 2, 2020 at 15:07
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The second to is both redundant and wrong. Yes, you have to drop it.

You note yourself that there are simpler ways of phrasing these constructions. But as they are phrased, they sound not just overly formal but virtually archaic! Nobody speaks or writes like that any more except for effect.

Although I am a believer in using whom, this is one of those cases when the great majority of native English speakers would say:

Whoever they were sent to....
and
What month is the event being deferred to

True, this is about idiom and not about grammar.

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